Reaction of hindered phenols with diazomethane

Meek, John S.; Fowler, Joanna S.; Monroe, Pearle A.; Clark, Tom

doi:10.1021/jo01265a043

Cited by 13 publications

(6 citation statements)

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“…4-Fluoropropofol was synthesized as follows. 4-Nitro-2,6-diisopropylanisole (Meek et al, 1968;Chastrette et al, 1986): 2,6-Diisopropylanisole (760 mg, 4 mmol) was dissolved in chloroform (5 mL) and treated with potassium nitrate (456 mg, 4.56 mmol) and trifluoroacetic anhydride (2 mL). The flask was loosely stoppered, and the mixture was stirred at room temperature for 5 days.…”

Section: Tables Of Linksmentioning

confidence: 99%

Activation and modulation of recombinant glycine and GABA_A receptors by 4‐halogenated analogues of propofol

Germann

Shin

Manion

et al. 2016

British J Pharmacology

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Section: Tables Of Linksmentioning

confidence: 99%

Activation and modulation of recombinant glycine and GABA_A receptors by 4‐halogenated analogues of propofol

Germann

Shin

Manion

et al. 2016

British J Pharmacology

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“…Nitronic esters are a relatively little studied group of compounds formally derived from aci -nitro compounds (or nitronic acids). Nitronic esters have been obtained mainly by three methods: (1) reaction of nitro compounds that are comparatively strong acids with diazomethane, (2) treatment of the silver salts of nitro compounds with alkyl iodides, utility being strained due to the observed instability of these silver salts, and (3) alkylation of the alkali metal salts of nitro compounds with trialkyloxonium fluoroborates and dimethyl sulfate 1a,5 (Scheme ). In addition, two special approaches are used for the preparation of nitronic esters from 2,6-di- tert -butyl-4-nitro phenol and trinitro methyl iodide…”

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confidence: 99%

Synthesis and Characterization of Chiral Nitronic Esters via O-Alkylation of (4S*,5R)-(+)-4-(1‘-Nitro-1‘-carbethoxymethyl)- 5-[(1R)-menthyloxy]-3,4-dihydro-2(5H)-furanone with Alkyl Halides

Kang

Yin

She³

1996

J. Org. Chem.

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A series of stable and enantiomerically pure alkyl nitronic esters are synthesized in good to excellent yields via O-alkylation of (4S*,5R)-(+)-4-(1‘-nitro-1‘-carbethoxymethyl)-5-[(1R)-menthyloxy]-3,4-dihydro-2(5H)-furanone (4a) with alkyl halides in the presence of K2CO3 and DMF at room temperature. Thus, nitronic esters are obtained for the first time from the alkali metal salt of a nitro compound and various alkyl halides, which refutes the traditionally held view that the reaction of alkyl halides with alkali metal derivatives of nitro compounds gives a carbonyl compound and an oxime, rather than a nitronic ester. Secondary alkyl nitronic esters are found to partially decompose into O-alkyloximes. The configurations of the nitronic esters and O-alkyloximes were assigned to be Z on the basis of the NOE experiments. The synthesis of the nitro furanone 4a and its enolization to form a six-membered intramolecular hydrogen bond structure are described.

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“…Alkyl nitronic esters can be prepared via the reaction of nitronic acids with diazomethane. [37] However, the more prevalent way of making alkyl nitronic esters is through deprotonation of a nitroalkane followed by alkylation of the resulting nitronate with alkyl halides, (e.g., 34 fi 35, Scheme 10). [38] A related synthetic method involves treatment of the nitronate with trialkyloxonium fluoroborates.…”

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confidence: 99%

Product Class 14: Nitronic Acids and Their Derivatives

Padwa¹,

Bellus²

2005

Category 4. Compounds With Two Carbon Heteroatom Bonds

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Previously published information regarding this product class can be found in Houben-Weyl, Vol. E 14b, pp 780-960. In addition, three books [1][2][3] and five book chapters/reviews [4][5][6][7] covering the relevant topics have been published. Alkylideneazinic acid is the standard IUPAC nomenclature for this class of compounds. However, nitronates, aci-nitro compounds, nitronic acids, and nitronic esters are still used in this context because the IUPAC nomenclature is not as widely adopted as these common names. Where applicable, specific compounds are named using the aci-nitro prefix.Nitronates are not common because they are very labile, even at room temperature. They readily decompose when mixed with either acid or base. Thus, their applications have usually been limited to use as transient intermediates. Nevertheless, stable nitronic acids and silyl nitronates have been isolated and characterized, and their potential use in synthesis is attracting more and more attention from synthetic chemists.With regard to synthetic applications, nitronic acid is the intermediate in the Nef reaction, which is employed to convert nitroalkanes into carbonyl compounds. Nitronate salts, on the other hand, serve as nucleophiles in nitroaldol condensation reactions (e.g., the Henry reaction). More importantly for organic synthesis, nitronic esters and silyl nitronates are widely used in 1,3-dipolar cycloaddition reactions with dipolarophiles. These [3 + 2] cycloadducts provide a useful entry to heterocycles.

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Reaction of hindered phenols with diazomethane

Cited by 13 publications

References 1 publication

Activation and modulation of recombinant glycine and GABA_A receptors by 4‐halogenated analogues of propofol

Activation and modulation of recombinant glycine and GABA_A receptors by 4‐halogenated analogues of propofol

Synthesis and Characterization of Chiral Nitronic Esters via O-Alkylation of (4S*,5R)-(+)-4-(1‘-Nitro-1‘-carbethoxymethyl)- 5-[(1R)-menthyloxy]-3,4-dihydro-2(5H)-furanone with Alkyl Halides

Product Class 14: Nitronic Acids and Their Derivatives

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Reaction of hindered phenols with diazomethane

Cited by 13 publications

References 1 publication

Activation and modulation of recombinant glycine and GABAA receptors by 4‐halogenated analogues of propofol

Activation and modulation of recombinant glycine and GABAA receptors by 4‐halogenated analogues of propofol

Synthesis and Characterization of Chiral Nitronic Esters via O-Alkylation of (4S*,5R)-(+)-4-(1‘-Nitro-1‘-carbethoxymethyl)- 5-[(1R)-menthyloxy]-3,4-dihydro-2(5H)-furanone with Alkyl Halides

Product Class 14: Nitronic Acids and Their Derivatives

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Activation and modulation of recombinant glycine and GABA_A receptors by 4‐halogenated analogues of propofol

Activation and modulation of recombinant glycine and GABA_A receptors by 4‐halogenated analogues of propofol